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Molecules 2016, 21(1), 45;

Improved Schmidt Conversion of Aldehydes to Nitriles Using Azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-propanol

Department of Medicinal Chemistry, Delbert M. Shankel Structural Biology Center, University of Kansas, 2034 Becker Drive, West Campus, Lawrence, KS 66047, USA
Author to whom correspondence should be addressed.
Academic Editor: Klaus Banert
Received: 5 November 2015 / Revised: 16 December 2015 / Accepted: 22 December 2015 / Published: 29 December 2015
(This article belongs to the Special Issue Organic Azides)
Full-Text   |   PDF [16507 KB, uploaded 29 December 2015]   |  


The Schmidt reaction of aromatic aldehydes using a substoichiometric amount (40 mol %) of triflic acid is described. Low catalyst loading was enabled by a strong hydrogen-bond-donating solvent hexafluoro-2-propanol (HFIP). This improved protocol tolerates a broad scope of aldehydes with diverse functional groups and the corresponding nitriles were obtained in good to high yields without the need for aqueous work up. View Full-Text
Keywords: Schmidt reaction; aldehydes; nitriles; HFIP Schmidt reaction; aldehydes; nitriles; HFIP

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Motiwala, H.F.; Yin, Q.; Aubé, J. Improved Schmidt Conversion of Aldehydes to Nitriles Using Azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-propanol. Molecules 2016, 21, 45.

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